EP0002222B1 - Aralkylpiperidinone und deren Anwendung als Fungizide - Google Patents

Aralkylpiperidinone und deren Anwendung als Fungizide Download PDF

Info

Publication number
EP0002222B1
EP0002222B1 EP78101404A EP78101404A EP0002222B1 EP 0002222 B1 EP0002222 B1 EP 0002222B1 EP 78101404 A EP78101404 A EP 78101404A EP 78101404 A EP78101404 A EP 78101404A EP 0002222 B1 EP0002222 B1 EP 0002222B1
Authority
EP
European Patent Office
Prior art keywords
parts
dimethyl
weight
acid
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP78101404A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0002222A1 (de
Inventor
Norbert Dr. Goetz
Walter Dr. Himmele
Bernd Dr. Zeeh
Ernst-Heinrich Dr. Pommer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0002222A1 publication Critical patent/EP0002222A1/de
Application granted granted Critical
Publication of EP0002222B1 publication Critical patent/EP0002222B1/de
Expired legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D211/74Oxygen atoms

Definitions

  • the present invention relates to valuable new aralkyl-3,5-dimethyl-piperidin-4-ones and their salts, fungicides containing these compounds and methods for combating fungi with these compounds.
  • the N-substituted 3,5-dimethylpiperidin-4-ones according to the invention can be prepared by reacting the corresponding primary amines with 2,4-dimethy) penta-1,4-dien-4-one: where R and X have the meaning given above.
  • the required primary amines can be prepared by reductive amination from the corresponding aldehydes or ketones (Houben-Weyl "Methods of Organic Chemistry", Volume 11/1, p. 602 ff).
  • the 2-methyl-3- (p-tert-butylphenyl) propylamine can be prepared, for example, according to the following procedure.
  • reaction product is then filtered and the filtrate is worked up by distillation.
  • you get 750 pieces ( 93% of theory) 2-methyl-3- (p-tert-butylphenyl) propylamine, bp 0.01 97 ° C.
  • the active compounds according to the invention and the corresponding fungicides are particularly suitable for controlling plant diseases, e.g. Erysiphe graminis (powdery mildew) on cereals, Erysiphe cichoriacearum (powdery mildew) on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Erysiphe polygoni on beans. Sphaerotheca pannosa on roses, Microsphaera querci on oaks. Mycosphaerella musicola on bananas, Puccinia species (rust fungi) on cereals, Uromyces appendiculatus and U. phaseoli on beans, Hemileia vastatrix on coffee and Rhizoctonia solani. They are systematically effective; they are absorbed both via the roots and the leaves and transported in the plant tissue.
  • plant diseases e.g. Erysiphe graminis (powdery mildew
  • the application rates are between 0.025 and 5 kg of active ingredient / ha area.
  • the active ingredients can also be used in conjunction with 0.25% to 5% plastic dispersions, based on the weight of the dispersion.
  • the fungicides generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the application is e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or pouring.
  • the application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, also coal tar oils etc., as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, are used to produce directly sprayable solutions, emulsions, pastes and oil dispersions.
  • Xylene paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, for example methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone etc., strongly polar solvents, for example Dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc. into consideration.
  • Aqueous use forms can be prepared, for example, emulsion concentrates, pastes or wettable powders (wettable powders), oil dispersions by adding water.
  • emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil which are suitable for dilution with water.
  • Powders, materials for spreading and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are e.g. Mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • Mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite
  • Oils of various types, herbicides, fungicides, nematocides, insecticides, bactericides, trace elements, fertilizers, anti-foaming agents (e.g. silicones), growth regulators, antidote agents or other active compounds can be added to the mixtures or individual active compounds.
  • Leaves of potted wheat seedlings of the "Jubilar” variety are sprayed with aqueous emulsions of 80% (weight percent) active ingredient and 20% emulsifier and, after the spray coating has dried on, are dusted with oidia (spores) of the powdery mildew (Erysiphe graminis var. Tritici).
  • the test plants are then placed in a greenhouse at temperatures between 20 and 22 ° C and 75 to 80% relative humidity. After 10 days, the extent of the development of mildew is determined.
  • Leaves of wheat plants grown in pots are artificially infected with spores of the wheat brown rust (Puccinia recondita) and placed in a steam-saturated chamber for 48 hours at 20 to 25 ° C.
  • the plants are then sprayed with aqueous spray liquors which contain a mixture of 80% of the active ingredient to be tested and 20% sodium lignosulfonate in the water or emulsified and in a greenhouse at temperatures between 20 and 22 ° C. and at 75 to 80% relative atmospheric humidity set up. After 10 days, the extent of the rust fungus development is assessed.
  • active ingredient 2 20 parts by weight of active ingredient 2 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic acid, 17 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill.
  • a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
  • active ingredient 1 40 parts by weight of active ingredient 1 are intimately mixed with 10 parts of sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water. A stable aqueous dispersion is obtained. Dilution with 100,000 parts by weight of water gives an aqueous dispersion which contains 0.04% by weight of active ingredient.
  • active ingredient 2 20 parts are intimately mixed with 2 parts of calcium salt of dodecylbenzenesulfonic acid, 8 parts of fatty alcohol polyglycol ether, 2 parts of sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP78101404A 1977-11-30 1978-11-18 Aralkylpiperidinone und deren Anwendung als Fungizide Expired EP0002222B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772753278 DE2753278A1 (de) 1977-11-30 1977-11-30 Aralkylpiperidinone
DE2753278 1977-11-30

Publications (2)

Publication Number Publication Date
EP0002222A1 EP0002222A1 (de) 1979-06-13
EP0002222B1 true EP0002222B1 (de) 1980-05-28

Family

ID=6024923

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78101404A Expired EP0002222B1 (de) 1977-11-30 1978-11-18 Aralkylpiperidinone und deren Anwendung als Fungizide

Country Status (3)

Country Link
EP (1) EP0002222B1 (cs)
CS (1) CS199223B2 (cs)
DE (2) DE2753278A1 (cs)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3634394A4 (en) * 2017-05-15 2021-04-07 Cognition Therapeutics, Inc. COMPOSITIONS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA792242B (en) * 1978-05-16 1980-05-28 Hoffmann La Roche Heterocyclic compounds
IT1291673B1 (it) * 1997-04-28 1999-01-19 Bracco Spa Processo per la preparazione di 1,4,7,10 - tetraazaciclododecano
GB2493327B (en) 2011-07-05 2018-06-06 Skype Processing audio signals
GB2495472B (en) 2011-09-30 2019-07-03 Skype Processing audio signals
GB2495131A (en) 2011-09-30 2013-04-03 Skype A mobile device includes a received-signal beamformer that adapts to motion of the mobile device
GB2495129B (en) 2011-09-30 2017-07-19 Skype Processing signals
GB2495130B (en) 2011-09-30 2018-10-24 Skype Processing audio signals
GB2495128B (en) 2011-09-30 2018-04-04 Skype Processing signals
GB2495278A (en) 2011-09-30 2013-04-10 Skype Processing received signals from a range of receiving angles to reduce interference
GB2496660B (en) 2011-11-18 2014-06-04 Skype Processing audio signals
GB201120392D0 (en) 2011-11-25 2012-01-11 Skype Ltd Processing signals
GB2497343B (en) 2011-12-08 2014-11-26 Skype Processing audio signals
JP6517827B2 (ja) 2014-01-31 2019-05-22 コグニション セラピューティクス,インコーポレイテッド イソインドリン組成物および神経変性疾患の治療方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3634394A4 (en) * 2017-05-15 2021-04-07 Cognition Therapeutics, Inc. COMPOSITIONS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES

Also Published As

Publication number Publication date
CS199223B2 (en) 1980-07-31
DE2860025D1 (en) 1980-10-16
EP0002222A1 (de) 1979-06-13
DE2753278A1 (de) 1979-05-31

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